


Just Like A Dream

by awriter_fromspace



Category: Supernatural
Genre: Anal Fingering, Begging Sam Winchester, Blow Jobs, Bottom Sam Winchester, Come Eating, Come Swallowing, Crossdressing, First Time, First Time Blow Jobs, French Maid Sam Winchester, M/M, Orgasm Delay/Denial, Plot What Plot/Porn Without Plot, Sam Winchester Likes It Rough, Top Dean Winchester, Top Dean Winchester/Bottom Sam Winchester, Wincest - Freeform, no foreplay, rough
Language: English
Status: Completed
Published: 2020-08-17
Updated: 2020-08-17
Packaged: 2021-03-06 02:21:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,903
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25945765
Author URL: https://archiveofourown.org/users/awriter_fromspace/pseuds/awriter_fromspace
Summary: When Dean breaks his computer again, Sam decides to do some snooping and finds Dean's *obsession* with French maids. Sam takes it as an opportunity to surprise Dean and do something with his brother he's always wanted to do.Mainly pwp, first time, crossdressing, rough, oral, fingering, come denial.
Relationships: Dean Winchester & Sam Winchester, Dean Winchester/Sam Winchester, Top!Dean/Bottom!Sam - Relationship
Comments: 4
Kudos: 172





	Just Like A Dream

It takes Dean totally by surprise in the best way possible. He has just returned from a supply run and nearly falls down the stairs when he finally sees it. Sam is cleaning in the library, dusting bookshelves taller than him, which is hard to achieve. At first, Dean thinks Sam hasn't noticed him, and he wants to preserve the moment, so he does his best to sneak up to him. 

Up close, he can appreciate every detail. The duster he's reaching up to use, every inch of skin it exposes, but most of all, the tiny skirt that shows off almost everything. 

"Hey, Dean."

For the second time, Dean almost falls flat on his face. 

"H-heya Sammy."

Sam turns toward him slowly and gives him a breathy little half-smile, nervous even now, "hey."

Dean takes the time to look him up and down, to appreciate his outfit. Sam is in a lace, black and white top, and the matching pouffy skirt falls just below that tight little ass. He's itching to slide his hands under it. 

"Sammy, why..." he's not sure how to finish, still mostly mesmerized by his little brother. 

"Well," Sam smiles awkwardly, "ah, you remember last time you broke my laptop? After I recovered it I... got a little curious, so I went through the internet history. And apparently, you really like french maids." He half shrugs and shuffles around a bit, still slightly uncomfortable. 

Dean's too amazed to be embarrassed. "Uh, can I?" He reaches toward the skirt tentatively, his heart racing. Dean has always felt something between him and his brother. A current of electricity always running under the surface. But neither of them has ever acted on it, in fact, Dean does his best to pretend it doesn't exist. The closest to even thinking about it that he has ever come is the odd dream, which he does his damnedest to repress. So this... this game they're playing is dangerous. Dean knows, logically, he should be cautious, hell he should run in the opposite direction. But it's intoxicating. Watching, in front of him, a dream come to life. 

"Yeah," Sam breathes out, which really only stokes the fire. 

Dean has every intention to be subtle, to slowly work his way up Sam's thighs but, instead, he finds his hands automatically sliding under Sam's skirt and over his ass. Sam's stutter of a breath does nothing but edge Dean on and before he knows it he's groping Sam all too desperately. 

Sam grunts and whispers something to him, before leaning in and kissing him. And Dean forgets every reason he's ever had to not kiss Sam, to not start something with him. 

It's slow and desperate, Sam's hands coming up to leave bruises on Dean's shoulders, Dean's hands leaving similar marks on Sam's ass. It's a long time before they pull away and when they finally do they're both gasping, hardly able to breathe.

Forehead to forehead, when Sam finally catches his breath he whispers, "Dean... please?"

Dean nods vigorously, "fuck, yes, Sammy."

He hastily pulls down his jeans and boxers, letting them pool at his ankles, not bothering to undress fully and grabs Sam's skirt, not able to resist lifting it up. He sucks in a big breath, feels, for a moment, like he can't get enough air. Sam is wearing red, lace undies, a thong, to be exact, and Dean can't take his eyes away from it. Instinctively he reaches out with his other hand to rub against Sam's straining dick, trapped in the lace fabric. Sam moans and pushes into his hand.

"Please, Dean, please." Demanding now.

Dean blinks rapidly, trying to get his vision to focus. Then he flips Sam around, forces him to face the wall of books, lifting his skirt again to run his finger over his hole, rubbing the thin fabric of the thong against it. 

"It's gonna hurt, Sam." He sighs.

Sam nods and tries to look over at him. "I'm prepared."

Which Dean doesn't understand until he pulls the scrap of fabric away to finds Sam's ass hole glistening. 

"You were ready for this?"

He chuckles lightly, "yeah. What did you think was gonna happen, Dean?"

Dean nods, he should have known that Sam expected this the moment he saw the outfit. But it was a lot to process at the time. Even now he can't believe this is really happening so, before he can wake up, he grabs himself and lines up to Sam's wet hole. Pushes against the little pucker until the tip of his dick pops into the tight heat of his brother, making them both moan. Dean brings his hands up to grip Sam's hips and slowly pushes further in.

A small groan of pain escapes Sam's lips and Dean has to put all his concentration on stopping, hands gripping harder, leaving bruises on his hips.

"Sammy....?" He can barely get it out, has trouble thinking of anything more than Sam surrounding him. 

But his brother groans again, deeper this time, "d-don't stop, just... just keep going, please."

Dean has his head between Sam's shoulder blades and, at the request, his hands move lower to spread Sam's ass cheeks, forcing one of Sam's hands back to hold up his skirt, wanting to watch as he pushes the rest of the way in. Dean's balls slap lightly against Sam's ass when he bottoms out and Dean has to shut his eyes for a moment, hardly breathing. Sam moans loudly, then, a shiver running through him, impatiently trying to fuck back against Dean despite the sting of his brother's big dick stretching him open. 

Dean takes a deep breath before pulling out almost entirely, then slamming back in, deep and trying to push deeper. Sam whimpers at the feeling, too much all at once, but Dean draws back and shoves in again with the same force, setting a relentless pace. Dean's dreams, the ones he tries so desperately to forget, plague his sleep and are so vivid he's been having trouble telling the difference between dreams and reality lately. His head is swimming and it isn't until Sam gives another groan of pain that he stops thrusting, halfway into him.

"Sammy, I'm sorry, I'm sorry. I'm so sorry, baby." Dean can't stop the apology, trailing kisses over Sam's shoulders.

But Sam's not happy, lifts his head and lets it fall back against Dean. "No, no, no, no, shut up, Dean. Keep going. Please." Whining again.

"Fuck, so demanding." Dean was sure his dreams would never translate into reality but this, this is real. And so much better. He hooks a hand under Sam's knee and pushes it up onto one of the shelves, giving him a better angle. Breathes into his brother's ear, "you're a little whore for me, aren't you, Sammy?"

Sam shivers, nods vigorously, "yes, Dean."

Dean grins against Sam's skin, bites lightly at his shoulder but doesn't move. Holds Sam in place as he tries to wiggle back against him, trying to get Dean all the way back in. Sam groans his name, somewhere between annoyed and frustrated, and Dean answers with a chuckle.

"Say it, Sammy."

Another frustrated groan. "I'm... I'm your little whore, Dean."

Dean moves one arm to wrap around Sam's waist, pulling him back as he slams forward again, knocking the air out of Sam. Dean's bruising pace is back and Sam can't find a moment to catch his breath. Stutters out Dean's name with every thrust.

Suddenly Sam throws his head back, moaning as Dean finds his prostate. His back arches, grinding his hips back against Dean, trying to hold him there. 

"F-fuckkk." Sam's hand drops to stroke himself but Dean catches his wrist and forces it back up.

"Don't worry, Sammy, I'll take care of that." Dean half whispers, half growls into his ear, sending shivers racing down Sam's spine. But when Dean reaches down, hand slipping into the lace undies, it's not to jack him off, grabs the base of Sam's dick instead and squeezes.

Sam's about to ask what the hell his brother's doing when Dean gives a few more thrusts, hitting that perfect spot every time and the air is punched out of his chest again. Dean keeps going, slamming into Sam, relentlessly chasing his own orgasm. It's not long before Sam's a mess under him, body rigid with the need to come. When Sam starts begging, Dean's name falling from his lips like a prayer, Dean loses it, can't hold it in anymore, coming hard and deep inside his brother. Dean's moans are drowning out all other noises, right in Sam's ear, and a darkness creeps into the edges of his vision, threatening to take over as Dean continues to fill him with his seed.

Sam is almost crying, shaking violently now, but Dean still won't let him come. Dean waits until he's caught his breath before pulling out with a pop, quickly trying to move them to keep his promise to Sam. Sam's heaving into his arms, face hidden, and Dean shushes him lightly, coming to kneel in front of him. With his free hand, he roughly pulls at Sam's thong, gives him a hurried apology for making him wait so long before ducking under the skirt and sucking down Sam's length, down to where his hand is still gripping the base. Sam keens, hips bucking forward into Dean's mouth.

Sam is begging again, desperately fucking himself against Dean. But Dean wants to give him a little more, pushes three fingers deep into Sam's ass, and finally lets go of Sam's dick. The loss lets Sam push his whole length into Dean's mouth, tip bumping against Dean's throat at the same time that his brother's searching fingers finally brush against Sam's sweet spot, and suddenly Sam is coming down Dean's throat. Sam moans out Dean's name, the earlier darkness fully taking over his vision, shaking him apart even as he drowns in the feeling.

Sam gasps awake, held up mainly by the bookcase in front of him, Dean still sucking the last of his orgasm out of him. He breathes deep, shivery, and carefully tries to pull away from Dean, who moans lightly as he pulls out. Dean's just as careful when he pulls out his fingers, breathing harshly.

"Fuck, Sammy." He breathes out, eyes looking up and locking with Sam's.

Sam doesn't know why but it makes him blush, Dean's lips bright red and come slicked, and he's already opening his own mouth, wanting to taste Dean's come, too. Eyes going dark just thinking of licking it off his fingers. It takes Dean a moment to understand but when he does, his breath hitches, lifting his fingers to Sam. He has to kneel down to reach comfortably, eyes closing and humming when the tangy, sticky liquid finally hits his tongue. Sam moans as he licks his brother's fingers clean and is pleased to see the dark stare Dean is giving him when they pull away.

Dean takes a deep, rattling breath, spit-soaked fingers moving to caress Sam's cheek. "You're so perfect, Sammy."

Sam chuckles and moves closer, buries his face into Dean's shoulder. Dean shifts them until Sam is seated fully in his lap, as comfortable as they're going to get down here. His brother sighs again, presses a long kiss to Sam's hair before whispering into it, "thank you, Sammy."

**Author's Note:**

> Thanks for reading this far! I hope you all enjoyed it! Kudos are love <3 Comment if you want to ^.^
> 
> The title is from the song: Just Like Heaven by The Cure (but I was listening to the Post Modern Jukebox cover, lol)


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